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Non-writers and non-freelancers sometimes have the misconception that independent workers work only when they want and exclusively on the projects that interest them. For those just starting to branch into freelancing–hopefully you don’t have this preconceived notion!

This month marks the 6-year anniversary of my resignation from 9-to-5 life, and this summer is Write Naked’s 5th Blogaversary! I had a few experiences the past few days and months that were a bit jarring. Why, after all this time, am I still experiencing the same struggles (albeit to much less a degree)?

Press preview invitations, working from anywhere, and the flexibility of freelancing are glamorous to me. With these perks come fugly features:

  1. Working the weekends. As of this writing, I haven’t had a day off in a little over two weeks. When I first started my writing business, days off were nonexistent. I’ve developed a work-life balance over the years and recently it’s been disrupted by new projects, deadlines, and events. Now that I’ve temporarily fallen back in this old routine of working the weekends I keep thinking, How did I do this?!
  2. Prove yourself. If you’re still a 9-to-5er, how much do you enjoy job searching, applying for positions, and the interview process? How often do you have to do it? Maybe once every few years? As a freelancer, if you are making new connections you constantly have to prove yourself. Fortunately, I have a few long-time anchor clients who know and trust me. I don’t regularly seek new work like I should. I am comfortable with the volume I’m managing that comes to me organically via online search, referrals, and events. However, I’ve written 13 proposals since January 1st. One was a returning past client, one was a friend, five were referrals. Although I did need to prove myself a bit with the referrals–having that trusted personal recommendation is a plus. The other half of the proposals I created were for individuals/organizations I had no prior relationship with. I have to educate them on online search so that they understand what my work involves and set expectations with project delivery. Earlier this year I made a typo on a blog post for a client I’ve had for nearly five years. They were not miffed by the error because they know that’s not the norm for me. However, if my first draft to a new client has a typo–that sets the wrong impression, much more pressure!
  3. PITA. I like the PITA factor, a variable I first saw described in Kelly James-Enger’s book Six-Figure Freelancing. The Pain-In-The-Ass factor is a number I mentally assign to every prospect. Is the work with the hassle? Generally I turn away all high PITA scorers. I recognized a high PITA prospect last fall and turned it down. I recognized another one earlier this year, but before I knew it I was accepting payment! Fortunately, I had told the client outright when we met that due to their defensive and negative behavior I was concerned they would be dissatisfied with my work no matter what I delivered. My prediction was true. The extra unnecessary effort involved to coddle this particular client interrupted my other work, laced stress into my personal time, and was a sour experience for all. Through the clarity of hindsight: I would have rather paid them the entire project fee upfront to make them stay away.

Overall, even though articles wrap up by deadline and go to print and new websites launch with engaging content, work is never done. There is always something that needs to be done.

travel blogger

The most unglamorous side of freelancing is that the pressure is always on. Think your finished? You could be pitching an article, ghostwriting a blog, submitting a proposal to speak at a conference, or getting caught up on filing/accounting. But, you can do that from anywhere, so maybe it is a bit glamorous.